Travel – it's a minefield. Always last minute, always limited options and always hugely impactful if you make a mistake!

Questions are unavoidable. You have to get it right so you have to know what right is for them. Most importantly, what are they going there for? If they miss it the whole trip is a waste. Work back from there.

There are so many components to research, not to mention all of your boss’s requirements particular just to them. I once worked with a guy who would only sit in specific seats on specific models of planes!

Before you bombard them with queries, make sure they are answerable with “yes” or “no” to avoid ambiguity and be certain you have covered all bases. You may be able to get information from other sources - colleagues, company travel policy, etc.

Build a bible for yourself so you get to the point where you can be confident making choices on your boss’s behalf. Things like: favourite airlines; preferred hotels; routes; seat choice; restaurants and so on. Have a debrief after every trip and update your bible accordingly. This can be hugely helpful when being covered as well.

Make a checklist so you can ensure nothing’s overlooked – you can then refer to this every time you have to arrange a trip.

Remember to adhere to company procedure – budget, cabin class, flex/non flex – often depends on purpose (internal/client facing), flight length, etc.

Always research everything – how long is the transfer between a) and b) – build in a bit of leeway. We have so many resources at our fingertips now. If your company has a travel agency use them but always double check! If you have to tell your boss something they don’t want to hear, for example you can’t fly direct, you must be confident as to why and 100% certain that’s the only option.

Some things to bear in mind that can get overlooked:

  • Take into account their personal life – do you need to include their partner in the itinerary? Are they travelling somewhere they have family so may be an idea to extend their stay to fit in a visit, etc.;
  • Use your colleagues. Others may well have done the same trip and have helpful info especially when it comes to things like the dreaded visas. Recommendations are invaluable;
  • If you have one, ask your local office for suggestions or the assistant of the client they are visiting. (If you go with their recommendation and the client gets billed for expenses your boss won’t look like they are taking the mickey swanning off to a more expensive hotel);
  • If you are booking for family travel as opposed to an individual remember there will be more luggage involved which will impact car requirements and so on;
  • If they are going to a conference but need to step out for a VC can you arrange a private place for them for that;
  • Do they need you to book the hotel the night before even though they will not arrive until the morning? (They might want to head there for a refresh before a meeting). Remember to always inform the hotel;
  • You might get really random requests when going to more obscure countries – private planes, personal security and others;
  • Do they want you to check in for them – are they old school and like printed boarding passes, itineraries, etc.;
  • Are any colleagues attending the same meeting or event? If so, it may well be useful for you to coordinate with their assistants and book the same hotel so they can prep over breakfast, or share transfers, get seats next to each other on the plane, (if they want to – they may want some peace!);
  • Do they need to take calls on the way to and from the airport;
  • If their team is involved are they staying at the same hotel? If they are in a four star and your boss is in a five star up the road consider the optics;
  • Do they prefer the quickest route or the smoothest route – for example are they ok jumping on the Heathrow Express or would they prefer a car;
  • Whilst your boss is wherever he/she is going to be, if they have time on their hands, it’s worth being proactive and checking in with other clients and contacts in the area to see if they happen to be able to catch up. My former boss once went to Houston for two meetings but had to be there for three days to accommodate them. I managed to get him in 13 client meetings during those days which he valued immensely;
  • If it’s a long journey, is it worth them going via somewhere? I knew of a guy who flew to Australia for a 30 minute meeting – no joke – might have been a better use of time if he had extended the trip slightly and tried to incorporate another meeting somewhere on the way;
  • Think outside the box – timings can seem impossible but how can you fast track things, for instance can you use a motorbike taxi? Have back up flights booked in case of missed connections, (obviously flexible and if budget allows);
  • Remember when scheduling calls whilst at airports it’s better to arrange five minutes when they are in an airport lounge than 15 when they are going through security and can’t focus or talk confidentially;
  • Passports – if they have two or more which one do you need the visa in? For example, if they are travelling to Saudi use one passport for that and the other for the US trips. It can avoid questions and complications – just make sure they take the right passport with them!;
  • Don’t forget to pre-book Wi-Fi for the plane, airport lounges and remember some countries still have COVID requirements so double check the regulations;
  • Push back – is it worth not only the cost but the time to take this trip? Would it be better to get a colleague in situ to go and your boss join virtually? Would it be more efficient to postpone to next week when they are already scheduled to be there and use this week to go somewhere else…;
  • You may have to tell them things they don’t want to hear. For instance, I can’t get you to Kazakhstan direct in business but I can in economy. There is nothing you can do other than research everything thoroughly and lay out all of the options once you have – the choice is then theirs;
  • Itineraries – what is your boss’s preference? What is easiest and most accessible for them? Do they favour paper based? Do they want all the information in their calendars and what info is most important for them;
  • Always be solutions focused – for example if there are no seats available on the flight they want put them on the waitlist. Try to find workarounds wherever you can or if you can’t do your best to make a positive out of a negative. E.g. You have a stopover in Singapore for seven hours but I have managed to book you a catch up with a client who is based there during that time;
  • If it’s a company event be careful to check your organisation’s procedure as it may be company policy not to allow all leadership on the same flight just in case of disaster;
  • Remember to keep an eye on the trip, are the planes on time, track cars, etc. If things are not running to plan what is the impact and how can you mitigate it? Call ahead to let people know things are running late, make sure pickups are aware of delays, and let your boss know you are on it and have covered all bases so they don’t panic. Be on hand.

The aim is to pre-empt travel and proactively book but it takes a trust-based relationship to get to that point. There is so much ground to cover and every individual we work for has their own quirks and preferences. It will all become second nature and, if you invest time and be conscientious when it comes to every detail, once you have a proven track record your boss can be 100% secure in the knowledge that you will formulate the right plan for them.

Helen Napoli